Process for producing thiamin



Patented Jan. 4, 1949 iJNiTED STATES PATENT OFFICE PROCESS FOR PRODUCING THIAMIN DERIVATIVES Kurt Warnat, Basel, Switzerland, assignor to Hoiimann-La Roche Inc., Nutley, N. J a corporation of New Jersey No Drawing. Application April 9, 1946, Serial No.

660,857. In Switzerland June 1, 1945' 1 Claim. (Cl. 260-251) 1 2 This invention relates to the manufacture of rated in vacuo and the crystalline residue disa thiamin derivative. solved with gentle heating in 25 parts by volume It is known that thiochrome is formed if potasof methyl alcohol. 200 parts by V e Of ac to e sium ferric cyanide is caused to act on an alkaline are added, a Small quantity of undiSSOlVed matesolution of aneurin. This reaction is used for the 5 rial immediately filtered Off and the filtrate analytical determination of thiamin (c. f. lowed to ystamze- Yield parts by weight I of the pure product. Melting point of the dry Gstirner "Chemische VitamimBestimmungsmesubstance: 177-179 C.

thoden, 3rd edition, year 1941, page 68, et seq.,

where further literature references are to be Example 2 g fifl P g Pfg fg gggai 20 parts by weight of thiamin are dissolved in ese Y' page 25 parts of Water, a cold solution of 5 parts by sltrpnsmgly enough has P been found weight of caustic soda in 25 parts of water added cordmg to the present mventlon that and the mixture oxidized with a solution of 2.4

pound of the following formula is obtained in 15 parts by weight of a stic soda and parts by predominant q y up acting potassium weight of potassium ferric cyanide in 80 parts of f ric y ni 0 the lk transformation water while stirring in the cold. The liquid is product of thiamin in concentrated solution: then evaporated to dryness in vacuo and the N-CH H3 OH: H N

In order to attain as far as possible complete oxidation product extracted with warm butyl alformation of the said compound, which is decohol. The butyl-alcoholic solution is evaporated scribed in German Patent Specification No. 749,- in vacuo and the residue dissolved with gentle 149, it is of advantage to provide for the reaction heating in parts by volume of methyl alcohol. solution always to contain at least 8 per cent of 39 100 parts by volume of acetone are added, the organic substance until the reaction is termisolution filtered and further quantities of nated; with increasing dilution of the reaction acetone added, whereupon crystallization sets in. mixture, the quantity of the thiochrome formed Yield: 12.2 parts by weight of the pure product,

as a by-product increases too. having the melting point 1'77179 C.

The disulfide manufactured in accordance with What I claim is: the present invention is to be employed as a A process which comprises mixing and reacting one mol of thiamin with three mols of caustic Example 1 soda and mixing and reacting the thiamin sodium salt thus obtained with one mol of potassium 10 P r y weight of thiamin are dissolved in 40 ferricyanide so as to produce a compound of the 15 parts of water, a cold solution of 3.7 parts by i n-owin formula:

medicinal preparation.

weight of caustic soda in 20 parts of water added while maintaining at least 8 per cent of organic and the mixture oxidised with solution of 10 substance in the reaction mixture throughout the parts by weight of potassium ferric cyanide in 0 reaction, Said Organic Substance being t 8 1 parts of Water while Stirring in the cold The plied by the aforementioned sodium salt and the d n 1 u a d final reaction product. liquid is then evaporated to ry ess n vac o n T WARNAT.

the oxidation product extracted with warm butyl alcohol. The butyl-alcoholic solution is evapo- No references cited. 

